With the news that Chicago’s Khalil Mack would miss the rest of the season with foot surgery, it seems like a good time—four seasons—to pass judgment on the Bears-Raiders trade that shook the NFL on Sept. 1, 2018. The Raiders traded Mack plus second-round and seventh-round picks (originally a conditional pick that turned out to be a seventh-rounder) to the Bears for two first-round picks and third-round and sixth-round choices.
It’s so interesting to analyze the trade. The Bears thought Mack would be the missing edge-rush piece they needed to chase and compete with the Packers in the NFC North. But since the trade, Chicago has zero playoff wins and is 1-6 head-to-head with the Packers. The Bears record in the seven Green Bay-Chicago meetings prior to the trade: 1-6. The Raiders got two useable offensive pieces out of the deal—Josh Jacobs and Bryan Edwards—but in all other ways for the franchise, the trade has been a disaster.
The scorecard:
• RAIDERS: The team used the first-round picks on Jacobs in 2019 and cornerback Damon Arnette in 2020, selected wideout Edwards with the third-round pick and used the sixth as a small piece in a trade that sent Kelechi Osemele to New York for a fifth-round pick. When the deal was made, Raiders coach Jon Gruden, who had personnel control of the franchise, said if you’re going to pay a quarterback like Derek Carr franchise-player money, you can’t also pay another player that kind of money and still build a strong roster. Not true, but the Raiders chose to spend the cap money they saved by not paying Mack on a slew of players acquired in the 2019 offseason who turned out to be crushing failures: Trent Brown, Antonio Brown, Lamarcus Joyner, Tyrell Williams. The Raiders got nothing but headaches with Antonio Brown, and wasted $85 million on Williams, Joyner and Trent Brown. Hmmm . . . $85 million. That’s about what it would have cost to keep Mack for these four seasons. Three failed players cost that much for two seasons.
Jacobs is a good NFL back, seventh in the league in rushing yards since being drafted. Edwards is a good piece on the Vegas receiver depth chart (32 catches in 1.5 years), middling value for a third-round pick. But overall, surrendering Mack and the 40th pick in the 2020 draft for massive cap room and two first-round picks should have yielded the backbone of a franchise. It hasn’t.

• BEARS: Mostly, they won the trade, because Mack’s production has been vital is lifting the Bears to third, eighth, 11th and 12th in yards allowed in his four seasons. And the added pick, tight end Cole Kmet, has been solid in his first 1.5 seasons. But the Bears have paid Mack $22.5 million a year in cash, on average. And, on average, Mack has been PFF’s 15th-rated edge-rusher over the past four years.
It’s hard to quantify how much a very good pass-rusher contributes to a team’s bottom line. After Mack’s infusion of energy and great play in 2018 lifted the Bears to the NFC North title, the Bears are 19-24 since. Certainly he can’t have the impact of, say, a quarterback, and he can’t make up for the Bears’ poor quarterback play in the last three seasons. But overall, I’d have expected more from the Bears than this combined record atop the NFC North since opening day 2018:
Green Bay, 42-20-1
Minnesota, 31-28-1
Chicago, 31-29
• MACK: Losers galore in this deal. One winner: Mack has played 54 games as a Bear—and made $90.1 million in these four seasons.
So many lessons:
1. Without a top-tier quarterback, acquiring a very good non-quarterback at any position is not enough to propel a team to greatness. So for the Bears, missing on Mitchell Trubisky was more of a negative for the franchise than acquiring Mack was a positive. Now the Bears will sink or swim on the Justin Fields pick.
2. The late George Young, when GM of the Giants, used to say, “Players don’t play better when you pay them more money.” Trent Brown was an okay tackle for New England in 2018. He was PFF’s 37th-rated tackle in 2018, playing for New England, allowing 37 sacks/hits/hurries of the quarterback. But the Raiders signed him to a four-year, $66-milion contract in 2019. He was a terrible investment, and reportedly undisciplined too; Vic Tafur of The Athletic reported he ballooned to 400 pounds while a Raider. The team paid him $37 million for two poor seasons—he missed 16 of 32 games due to injuries—then traded him back to New England. Investing in Trent Brown is a big reason why the Raiders gave up a top pass-rusher. These personnel mistakes make it difficult to build a team with a solid base.
3. Big trades pump energy into franchises that are treading water. But they can be fool’s gold without smart teams either building around a great new player, or using high picks to build a future. This offseason could be a period of unprecedented veteran QB trades. Deshaun Watson is likely to be dealt by Houston, and Aaron Rodgers and Russell Wilson might be traded too. So many of these trades—three or four high picks for a great player—look lousy for the team getting the bounty a few years down the road. The GM pulling the trigger, and the scouting infrastructure he has built, will be on the line. Houston GM Nick Caserio has never made a huge trade before, and he’s never had a single first-round or second-round pick, never mind a slew of them. There won’t be time for him to make rookie mistakes if he trades Watson.
4. Jimmy Johnson used to gather multiple picks. In most cases after the Cowboys drafted Troy Aikman first overall in 1989, Johnson would rather have had, say, the 30th and 45th picks instead of the 10th. He once told me he was more comfortable with more picks because he knew he was going to make mistakes in every draft. The Raiders were taking a chance with a character risk in 2020, Ohio State cornerback Arnette, with the 19th pick. Say they dealt that pick for similar value on the draft-trade value chart on draft weekend. The 19th pick has similar value, combined, to two Miami picks, 39 and 56. These are all pie-in-the-sky inventions, of course. But imagine the Raiders today, after using the 39th pick on cornerback Trevon Diggs of Alabama, and the 56th on linebacker Logan Wilson. Two reliable, long-term building blocks. My point: Unless it’s on a quarterback, I’m not taking character risks in the first round, ever.
Read more in Peter King’s Football Morning in America column